1-(5-Methyl-[1,2,4]oxadiazol-3-yl)-ethanone → HCID 58221804, compound

HRID 1398548Notes

Reaction equation

HRID 1398548 reaction equation
[C:1]([Mg]Br)#[CH:2].[CH3:5][C:6]1[O:10][N:9]=[C:8]([C:11](=[O:13])[CH3:12])[N:7]=1>C1COCC1>[CH3:5][C:6]1[O:10][N:9]=[C:8]([C:11]([OH:13])([C:1]#[CH:2])[CH3:12])[N:7]=1

Participants

4

Reactant 2

HCID 115064521-(5-Methyl-[1,2,4]oxadiazol-3-yl)-ethanoneHCID 178418486HCID 178418486, compound

Product 1

HCID 58221804HCID 58221804, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethynylmagnesium bromide (0.5 M in THF, 800 mL, 400 mmol) at 0° C. was added 1-(5-methyl-1,2,4-oxadiazol-3-yl)ethanone (33.5 g, 266 mmol) in THF (533 mL) slowly. The reaction was allowed to warm to room temperature and stirred for 5 hours. After being quenched with saturated NH4Cl (750 mL) at 0° C., the THF was removed in vacuo and the aqueous residue was extracted with ethyl acetate (600 mL×2). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to give dark brown oil. The dark brown oil was purified by silica gel column chromatography use 10% of ethyl acetate in hexanes as eluent to give the title compound (36 g, 89%), 1H NMR (CDCl3, 400 MHz): delta 3.93 (s, 1H), 2.63 (s, 1H), 2.61 (s, 3H), 1.91 (s, 3H).

Workup

  1. customAfter being quenched with saturated NH4Cl (750 mL) at 0° C.
  2. customthe THF was removed in vacuo
  3. extractionthe aqueous residue was extracted with ethyl acetate (600 mL×2)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give dark brown oil
  8. customThe dark brown oil was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4291d46a7a5e47f298967a44cc3a566b
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

Loading…